CN104356178B - Preparation method of glucosinolate and benzyl isothiocyanate as metabolite of glucosinolate - Google Patents
Preparation method of glucosinolate and benzyl isothiocyanate as metabolite of glucosinolate Download PDFInfo
- Publication number
- CN104356178B CN104356178B CN201410717306.9A CN201410717306A CN104356178B CN 104356178 B CN104356178 B CN 104356178B CN 201410717306 A CN201410717306 A CN 201410717306A CN 104356178 B CN104356178 B CN 104356178B
- Authority
- CN
- China
- Prior art keywords
- glucosinolate
- temperature
- extract
- benzyl isothiocyanate
- extraction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/22—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C331/24—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
The invention discloses a preparation method of glucosinolate and benzyl isothiocyanate as a metabolite of glucosinolate. The preparation method comprises the following steps: firstly carrying out supercritical CO2 extraction on enzyme-deactivated Maca powder to extract fat-soluble components, removing impurities such as sterol by a cold precipitation method, carrying out ethyl esterification on the grease in the extract by an enzyme-catalyzed alcoholysis method and finally carrying out two-stage molecular distillation to obtain benzyl isothiocyanate and glucosinolate. Since ethanol is only used as a solvent, the preparation method is safe, non-toxic, free of pollution and simple in process and the scale production is easily achieved.
Description
Technical field
The present invention relates to the preparation method of a kind of glucosinolate and its metabolite benzyl isothiocyanate, specifically goes out
Pueraria root powder after enzyme is initially with supercritical CO2Liposoluble constituent is extracted by extraction, and the impurity such as sterol are removed by then cold analysis
Fall, then will be the oils and fatss in extract ethyl esterified with enzyme catalysiss alcoholysis method, most after Jing two-stage molecular distillations obtain isothiocyanic acid benzyl
Ester and glucosinolate.The invention belongs to field of natural organic chemistry.
Background technology
Glucosinolate and its metabolite benzyl isothiocyanate are the important components of Lepidinm meyenii Walp, and they can be used as chemosynthesis
The succedaneum of estrogen.Separately there are some researches show that glucosinolate and its isosulfocyanate material have the work(of antagonism kinds cancer
Effect.
Benzyl mustard oil glycosides and meta-methoxy benzyl mustard oil glycosides have to the tumor of many tumors especially gastronintestinal system
Good preventive effect；Benzyl isothiocyanate has the biological activity of height, the such as effect such as sterilization, suppression platelet aggregation, to disliking
Sexual cell has selection inhibitory action, can reduce the danger that people suffer from pulmonary carcinoma, gastric cancer, carcinoma of prostate, bowel cancer, breast carcinoma.
Glucosinolate is more with organic solvent extraction, then acid treatment, last macroporous resin adsorption or adverse current chromatogram etc. at present
It is refined, a large amount of acid waste waters are produced in production process, great environmental pollution is easily caused, and is yielded poorly；Benzyl isothiocyanate
Extract and separation has no report.
The content of the invention
It is an object of the invention to overcome the deficiency of prior art, there is provided a kind of simple easily realization is continuous to produce glucosinolate
And its method for metabolite benzyl isothiocyanate.
The purpose of the present invention is to be achieved through the following technical solutions：
The preparation method of a kind of glucosinolate and its metabolite benzyl isothiocyanate, comprises the steps：
Step one：Supercritical CO2Extraction
Pueraria root powder after enzyme denaturing adopts supercritical CO2Extraction, extracting pressure are controlled between 15.0～24.0MPa, extraction
Temperature control between 46.0～65.0 DEG C, CO2Flow-control in per kilogram 15～30L/h of raw material, extraction 50.0min～
After 100.0min, separated to obtain extract, extraction terminates；
The separation adopts the second-order separation, flash trapping stage Stress control between 6.0～9.0Mpa, flash trapping stage temperature control
Between 30.0～50.0 DEG C, between 4.5～6.0Mpa, the second-order separation temperature control is 30.0 for the second-order separation Stress control for system
Between～50.0 DEG C.
Step 2：Cold analysis
First extract is dehydrated, then dehydration extract is mixed with dehydrated alcohol, with the cooling rate of 1.0～5.0 DEG C/h
Start to stir cold analysis, per 30.0～60.0min, 1.0～5.0min is stirred once, every time in stirring, when reach static cold analysis temperature-
When 10.0～5.0 DEG C, stop stirring, after static 6.0～24.0h of cold analysis, be removed by filtration the impurity such as sterol, obtain cold analysis liquid；
The dehydration extract and the mass ratio of dehydrated alcohol are：100:(60～200).
Step 3：Enzyme catalysiss alcoholysis
To in cold analysis liquid plus Novozym435 immobilized enzyme, reaction temperature control is between 30～60 DEG C；Stirring reaction 2～
After 6h, filter immobilized enzyme, by alcoholic solution recovered under reduced pressure after, obtain the alcoholysis liquid containing benzyl isothiocyanate and glucosinolate；
The mass ratio of the extract and immobilized enzyme is 100:(1～8).
Step 4：Three-level molecular distillation is separated
Alcoholysis liquid containing benzyl isothiocyanate and glucosinolate, Jing first order moleculars distillation, removes volatile component, two grades
Distillation obtains benzyl isothiocyanate, and three-level molecular distillation is removed fatty-acid ethyl ester, obtains glucosinolate；
First order molecular distillation vacuum is 50.0～100.0Pa, and one-level vapo(u)rizing temperature is 70.0～100.0 DEG C, one
5.0～10.0 DEG C of condensation temperature of level.
Secondary molecules distillation vacuum is 25.0～50.0Pa, and secondary distillation temperature is 100.0～130.0 DEG C, two
10.0～20.0 DEG C of condensation temperature of level.
The three-level molecular distillation vacuum is 5.0～25.0Pa, and three-stage distillation temperature is 140.0～180.0 DEG C, three-level
25.0～50.0 DEG C of condensation temperature.
The present invention is had the advantage that compared with prior art：
1st, the present invention adopts SCF-CO 2, and not only extraction temperature is low, and does not use solvent, extracts extraction process
Safety, it is nontoxic, it is to avoid effective ingredient receives heat damage.
2nd, the present invention adopts thtee-stage shiplock supercritical CO2Extraction, two kettles are in extraction state, and a kettle is in discharging, charging
State, is capable of achieving semi-continuous production, substantially increases production efficiency.
3rd, the present invention adopts enzyme catalysiss alcoholysis, it is to avoid cause the destruction of effective ingredient, work using the operation of the soda acids such as saponification
Without the need for washing during skill, and then glucosinolate hydrolysis is not resulted in, while producing without sewage such as soda acids yet.
4th, ethanol is only used as solvent in the present invention, thus it is safe and nontoxic, pollution-free.
5th, the present invention separates benzyl isothiocyanate and glucosinolate using molecular distillation, not only reduces high temperature to extract
The destruction of effective ingredient, and avoid organic solvent participation, product no solvent residue.
6th, the present invention can obtain accessory substance aliphatic acid second while product benzyl isothiocyanate and glucosinolate is obtained
Ester.
7th, not only yield is high for benzyl isothiocyanate of the present invention and glucosinolate, and product purity is high.
8th, process of the present invention is simple, and loss of material is low, easily realizes commercial production.
Description of the drawings
Fig. 1 is the process chart of the present invention.
Fig. 2 is the extraction equipment figure of the present invention.
Fig. 3 is benzyl isothiocyanate standard substance gas chromatogram.
Fig. 4 is 1 supercritical CO of the embodiment of the present invention2Extract gas chromatogram.
Fig. 5 is obtained benzyl isothiocyanate gas chromatogram for the embodiment of the present invention 1.
Specific embodiment
By following examples and its accompanying drawing, the present invention is described in further detail, but embodiments of the present invention are not
It is limited to this, for especially not dated technological parameter, can refer to routine techniquess is carried out.
Embodiment 1
A kind of preparation method of glucosinolate and its metabolite benzyl isothiocyanate, step and its condition it is as follows：
Step one：Three-level supercritical CO2Extraction
10.00kg Lepidinm meyenii Walp (contains benzyl isothiocyanate 3.54%, 4.05%) glucosinolate after microwave deactivating enzyme, is crushed to 100
Mesh, using thtee-stage shiplock supercritical CO2Extraction, as shown in Fig. 2 the extraction kettle 1 of three series connection, extraction kettle 2, extraction kettle 3 connect
The separating still 1 of two series connection, separating still 2, CO2Flow is 300L/h, and extracting pressure is 16.0MPa, and extraction temperature is 65.0 DEG C,
Flash trapping stage pressure is 6.5Mpa, and flash trapping stage temperature is 50.0 DEG C, and the second-order separation pressure is 4.5Mpa, and the second-order separation temperature is
50.0 DEG C, after extraction 100.0min, extract is released from separating still 1 and 2；Using thtee-stage shiplock supercritical CO2Extraction, two kettles
In extraction state, a kettle is in discharging, state of charge, is capable of achieving semi-continuous production, substantially increases production efficiency.
The step 2：Cold analysis
Extract point liquid is removed into water layer with separatory funnel, 1.11kg dehydration extracts is obtained, then to dehydration extract
Middle addition 0.70kg dehydrated alcohol, starts to stir cold analysis with the cooling rate of 4.0 DEG C/h, stirs once per 30.0min, stir every time
1.0min is mixed, when -5.0 DEG C of static cold analysis temperature is reached, stops stirring, after static cold analysis 6.0h, it is miscellaneous that sucking filtration removes sterol etc.
Matter, obtains cold analysis liquid；
Step 3：Enzyme catalysiss alcoholysis
Add 25.0g Novozym435 immobilized enzyme (Novozymes Company) in cold analysis liquid, controlling reaction temperature is 35.0
DEG C, after stirring reaction 6.0h, filter immobilized enzyme, by alcoholic solution recovered under reduced pressure after, obtain containing benzyl isothiocyanate and mustard oil
The alcoholysis liquid of glycosides.
Step 4：Molecular distillation is separated
Alcoholysis liquid containing benzyl isothiocyanate and glucosinolate is removed after volatile components Jing first order molecular distillation, bis- grades of Jing
Molecular distillation obtains 354.5g benzyl isothiocyanates, and (content is 80.23%, and extraction yield is 80.34%) Jing three-level molecular distillations
Fatty-acid ethyl ester is removed, (content is 74.51%, and 90.03%) total yield is to obtain 489.4g glucosinolates；
The first order molecular distillation vacuum is 50.0Pa, and one-level vapo(u)rizing temperature is 80.0 DEG C, one-level condensation temperature 5.0
DEG C, secondary molecules distillation vacuum is 25.0Pa, and secondary distillation temperature is 110.0 DEG C, 10.0 DEG C of B-grade condensation temperature, three fraction
Son distillation vacuum is 5.0Pa., and three-stage distillation temperature is 150.0 DEG C, 25.0 DEG C of three-level condensation temperature.
The glucosinolate content detection method is shown in NY/T1103.3 --- the measure of 2006 thioglycoside.
Embodiment 2
A kind of preparation method of glucosinolate and its metabolite benzyl isothiocyanate, except for the following differences, other steps
And its process conditions are with embodiment 1：
(1) step one：CO2Flow is 240L/h, and extracting pressure is 20.0MPa, and extraction temperature is 55.0 DEG C, extraction time
For 75.0min, flash trapping stage pressure is 7.5Mpa, and flash trapping stage temperature is 40.0 DEG C, and the second-order separation pressure is 5.0Mpa, two grades
Separation temperature is 40.0 DEG C, obtains 1.19kg dehydration extracts.
(2) step 2：The quality for adding dehydrated alcohol is 1.05kg, and intermittent stirring per 30.0min, once, stir every time by stirring
3.0min is mixed, intermittent stirring cooling rate is 3.0 DEG C/h, and static cold analysis temperature is 0.0 DEG C, and the static cold analysis time is 12.0h.
(3) step 3：The quality for adding immobilized enzyme is 60.0g, and reaction temperature is 45.0 DEG C, stirring reaction 4.0h.
(4) step 4：The first order molecular distillation vacuum is 80.0Pa, and one-level vapo(u)rizing temperature is 90.0 DEG C, and one-level is cold
8.0 DEG C of solidifying temperature, secondary molecules distillation vacuum are 35.0Pa, and secondary distillation temperature is 120.0 DEG C, B-grade condensation temperature 15.0
DEG C, three-level molecular distillation vacuum is 15.0Pa., and three-stage distillation temperature is 160.0 DEG C, and 35.0 DEG C of three-level condensation temperature is obtained
361.3g benzyl isothiocyanates (content is 81.09%, extraction yield be 82.76%) and 493.6g glucosinolates (content is
75.12%, 91.55%) total yield is.
Embodiment 3
A kind of preparation method of glucosinolate and its metabolite benzyl isothiocyanate, except for the following differences, other steps
And its process conditions are with embodiment 1：
(1) step one：CO2Flow is 180L/h, and extracting pressure is 24.0MPa, and extraction temperature is 46.0 DEG C, extraction time
For 50.0min, flash trapping stage pressure is 8.5Mpa, and flash trapping stage temperature is 30.0 DEG C, and the second-order separation pressure is 6.0Mpa, two grades
Separation temperature is 30.0 DEG C, obtains 1.25kg dehydration extracts.
(2) step 2：The quality for adding dehydrated alcohol is 1.20kg, and intermittent stirring per 60.0min, once, stir every time by stirring
5.0min is mixed, intermittent stirring cooling rate is 2.0 DEG C/h, and static cold analysis temperature is 5.0 DEG C, and the static cold analysis time is 18.0h.
(3) step 3：The quality for adding immobilized enzyme is 90.0g, and reaction temperature is 55.0 DEG C, stirring reaction 2.0h.
(4) step 4：First order molecular distillation vacuum is 100.0Pa, and one-level vapo(u)rizing temperature is 100.0 DEG C, one-level condensation
10.0 DEG C of temperature, secondary molecules distillation vacuum are 45.0Pa, and secondary distillation temperature is 130.0 DEG C, B-grade condensation temperature 20.0
DEG C, three-level molecular distillation vacuum is 25.0Pa, and three-stage distillation temperature is 175.0 DEG C, and 45.0 DEG C of three-level condensation temperature is obtained
367.7g benzyl isothiocyanates (content is 81.85%, extraction yield be 85.01%) and 490.9g glucosinolates (content is
75.46%, 91.46%) total yield is.
Claims (9)
1. a kind of preparation method of glucosinolate metabolite benzyl isothiocyanate, comprises the steps：
Step one：Supercritical CO2Extraction
Pueraria root powder after enzyme denaturing is adopted into supercritical CO2Extraction, extracting pressure are controlled between 15.0～24.0MPa, extraction temperature
Control between 46.0～65.0 DEG C, CO2Flow-control extracts 50.0min～100.0min in per kilogram 15～30L/h of raw material
Afterwards, it is isolated to extract；
Step 2：Cold analysis
First extract is dehydrated, then dehydration extract is mixed with dehydrated alcohol, started with the cooling rate of 1.0～5.0 DEG C/h
Stirring cold analysis, when -10.0～5.0 DEG C of static cold analysis temperature is reached, stops stirring, after static 6.0～24.0h of cold analysis, filters
After remove impurity, cold analysis liquid is obtained；
Step 3：Enzyme catalysiss alcoholysis reaction
To in cold analysis liquid plus Novozym435 immobilized enzyme, reaction temperature control is between 30～60 DEG C；2～6h of stirring reaction
Afterwards, filter immobilized enzyme, by alcoholic solution recovered under reduced pressure after, obtain the alcoholysis liquid containing benzyl isothiocyanate and glucosinolate；
Step 4：Molecular distillation is separated
Alcoholysis liquid containing benzyl isothiocyanate and glucosinolate, Jing first order moleculars distillation, removes volatile component, bis- fraction of Jing
Son distillation obtains benzyl isothiocyanate.
2. method according to claim 1, it is characterised in that separating described in step one includes flash trapping stage and two fraction
From, wherein flash trapping stage Stress control between 6.0～9.0Mpa, flash trapping stage temperature control between 30.0～50.0 DEG C,
, between 4.5～6.0Mpa, the second-order separation temperature control is between 30.0～50.0 DEG C for the second-order separation Stress control.
3. method according to claim 1, it is characterised in that stirring described in step 2 is stirred per 30.0～60.0min
Once, 1.0～5.0min is stirred every time.
4. method according to claim 1, it is characterised in that the quality of extract and dehydrated alcohol is dehydrated described in step 2
Than for：100:(60～200).
5. method according to claim 1, it is characterised in that the mass ratio of the dehydration extract and immobilized enzyme is
100:(1～8).
6. the method according to Claims 1 to 5 any one, it is characterised in that first order molecular distillation described in step 4
Condition：Vacuum is 50.0～100.0Pa, and vapo(u)rizing temperature is 70.0～100.0 DEG C, and condensation temperature is 5.0～10.0 DEG C.
7. method according to claim 6, it is characterised in that the condition of secondary molecules distillation described in step 4：Vacuum
For 25.0～50.0Pa, vapo(u)rizing temperature is 100.0～130.0 DEG C, and condensation temperature is 10.0～20.0 DEG C.
8. a kind of preparation method of glucosinolate, it is characterised in that four institute the step of any one method in claim 1～7
State alcoholysis liquid Jing three-level molecular distillations and remove fatty-acid ethyl ester, that is, obtain glucosinolate.
9. method according to claim 8, it is characterised in that the condition of the three-level molecular distillation：Vacuum be 5.0～
25.0Pa, vapo(u)rizing temperature are 140.0～180.0 DEG C, and condensation temperature is 25.0～50.0 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410717306.9A CN104356178B (en) | 2014-12-02 | 2014-12-02 | Preparation method of glucosinolate and benzyl isothiocyanate as metabolite of glucosinolate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410717306.9A CN104356178B (en) | 2014-12-02 | 2014-12-02 | Preparation method of glucosinolate and benzyl isothiocyanate as metabolite of glucosinolate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104356178A CN104356178A (en) | 2015-02-18 |
| CN104356178B true CN104356178B (en) | 2017-04-19 |
Family
ID=52523508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410717306.9A Active CN104356178B (en) | 2014-12-02 | 2014-12-02 | Preparation method of glucosinolate and benzyl isothiocyanate as metabolite of glucosinolate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104356178B (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1357370A (en) * | 2001-12-20 | 2002-07-10 | 华中科技大学 | Extraction process of effective component in Maka |
| CN1579222A (en) * | 2003-08-07 | 2005-02-16 | 酒井四郎 | Fractionation of allyl isothiocyanate, p-hydroxybenzyl-isothiocyanate, protein and fiber from mustard |
| CN101249110A (en) * | 2008-04-07 | 2008-08-27 | 四川省中医药科学院 | Volatile oil component extracting separation method of plants medicinal materials and application thereof |
-
2014
- 2014-12-02 CN CN201410717306.9A patent/CN104356178B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1357370A (en) * | 2001-12-20 | 2002-07-10 | 华中科技大学 | Extraction process of effective component in Maka |
| CN1579222A (en) * | 2003-08-07 | 2005-02-16 | 酒井四郎 | Fractionation of allyl isothiocyanate, p-hydroxybenzyl-isothiocyanate, protein and fiber from mustard |
| CN101249110A (en) * | 2008-04-07 | 2008-08-27 | 四川省中医药科学院 | Volatile oil component extracting separation method of plants medicinal materials and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| Glucosinolates and their breakdown products in food and food plants;G. Roger Fenwick，等;《CRC Critical Reviews in food science and nutrition》;19831231;第18卷(第12期);第123-201页 * |
| 新疆产玛咖的挥发油成分研究;金文闻，等;《食品科学》;20090615;第30卷(第12期);第242页左栏1.3 玛咖挥发油提取，第243页左栏 * |
| 玛咖药用价值与引种培育研究进展;王义强，等;《经济林研究》;20140630;第32卷(第2期);第167-172页 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104356178A (en) | 2015-02-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1102860C (en) | Process for fluid/dense gas extraction under enhanced solubility condition | |
| CN103073915B (en) | Process for extracting and separating capsanthin and capsaicin by using biological enzyme | |
| CA2830489C (en) | Chemical additives and use thereof in stillage processing operations | |
| DE60304407T2 (en) | Extraction of vitamin E, phytosterols and squalene from palm oil | |
| CN101531690B (en) | New technology for extracting tea saponin and tea seed oil from tea seeds by using water as solvent | |
| CN102432582A (en) | Preparation method of proanthocyanidin | |
| CN111892988B (en) | Ground sesame oil treatment process and sesame oil prepared by same | |
| CN115029180A (en) | Preparation method of emu oil | |
| CN101434973B (en) | Process for extracting anthocyanidin in blackcurrant by aqueous enzymatic method | |
| CN105566167B (en) | The recovery method of urea in a kind of urea job contract skill | |
| CN112679556B (en) | Production process of high-purity tea saponin | |
| CN101747659B (en) | Method for removing phospholipids from paprika oleoresin | |
| CN104356178B (en) | Preparation method of glucosinolate and benzyl isothiocyanate as metabolite of glucosinolate | |
| CN201744192U (en) | Dynamic extracting tank for producing tea polyphenol | |
| CN101417917B (en) | Method for preparing high-purity all-trans lycopene crystal | |
| CN108383702B (en) | Method for extracting citronellal from litsea cubeba head oil | |
| CN111072469A (en) | Method for extracting natural nervonic acid | |
| EP3858848B1 (en) | Method for preparing oryzanol by using soapstock containing oryzanol as raw material | |
| CN108219922A (en) | A kind of tea seed ready-mixed oil with healthcare function and preparation method thereof | |
| CN109528784B (en) | Method for extracting and preparing 4,4' -dimethyl sterol from shea butter | |
| CN102079883A (en) | Novel process for extracting capsanthin and chilli extract by composite solvent | |
| CN1557879A (en) | Process and device for extracting natural lycopene oil resin | |
| CN106890200A (en) | Extract method and the medicine containing squalene of plant source spiny dogfish ene compositions and its preparation method and application | |
| CN110724257A (en) | Method for extracting polyglycerol from glycerol slag | |
| CN101323814B (en) | Method for leaching cold press peeled vegetable seed cake oil by using mixed solvent |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20190124 Address after: 674100 Ciman Five Society, Huangshan Residential Committee, Shuhe Street, Gucheng District, Lijiang City, Yunnan Province Patentee after: Lijiang Yinghuangji Bioengineering Co., Ltd. Address before: 674100 Huangshan Neighborhood Committee of Shuhe Street, Ancient District of Lijiang City, Yunnan Province Patentee before: Lijing mill at the age of one hundred years old biotechnology development corporation, Ltd. |